WO2010125102A1 - 5,6,7,8-TETRAHYDRO[1,2,4]TRIAZOLO[4,3-a]PYRAZINE DERIVATIVES AS P2X7 MODULATORS - Google Patents

5,6,7,8-TETRAHYDRO[1,2,4]TRIAZOLO[4,3-a]PYRAZINE DERIVATIVES AS P2X7 MODULATORS Download PDF

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Publication number
WO2010125102A1
WO2010125102A1 PCT/EP2010/055715 EP2010055715W WO2010125102A1 WO 2010125102 A1 WO2010125102 A1 WO 2010125102A1 EP 2010055715 W EP2010055715 W EP 2010055715W WO 2010125102 A1 WO2010125102 A1 WO 2010125102A1
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Prior art keywords
carbonyl
triazolo
tetrahydro
pyrazine
chloro
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PCT/EP2010/055715
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English (en)
French (fr)
Inventor
David Kenneth Dean
Jorge Munoz-Muriedas
Mairi Sime
Jon Graham Anthony Steadman
Rachel Elizabeth Anne Thewlis
Giancarlo Trani
Daryl Simon Walter
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Glaxo Group Limited
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Publication date
Application filed by Glaxo Group Limited filed Critical Glaxo Group Limited
Priority to US13/266,592 priority Critical patent/US8501946B2/en
Priority to EP10720006.5A priority patent/EP2424869B1/en
Priority to JP2012507732A priority patent/JP5654001B2/ja
Priority to ES10720006.5T priority patent/ES2590987T3/es
Publication of WO2010125102A1 publication Critical patent/WO2010125102A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Neurosurgery (AREA)
  • Public Health (AREA)
  • Pain & Pain Management (AREA)
  • Psychology (AREA)
  • Rheumatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/EP2010/055715 2009-04-29 2010-04-28 5,6,7,8-TETRAHYDRO[1,2,4]TRIAZOLO[4,3-a]PYRAZINE DERIVATIVES AS P2X7 MODULATORS WO2010125102A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US13/266,592 US8501946B2 (en) 2009-04-29 2010-04-28 5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine derivatives as P2X7 modulators
EP10720006.5A EP2424869B1 (en) 2009-04-29 2010-04-28 5,6,7,8-TETRAHYDRO[1,2,4]TRIAZOLO[4,3-a]PYRAZINE DERIVATIVES AS P2X7 MODULATORS
JP2012507732A JP5654001B2 (ja) 2009-04-29 2010-04-28 Ｐ２Ｘ７調節因子としての５，６，７，８−テトラヒドロ［１，２，４］トリアゾロ［４，３−ａ］ピラジン誘導体
ES10720006.5T ES2590987T3 (es) 2009-04-29 2010-04-28 Derivados de 5,6,7,8-tetrahidro[1,2,4]triazolo[4,3-a]pirazina como moduladores de P2X7

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US17370109P 2009-04-29 2009-04-29
US61/173,701 2009-04-29

Publications (1)

Publication Number Publication Date
WO2010125102A1 true WO2010125102A1 (en) 2010-11-04

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PCT/EP2010/055715 WO2010125102A1 (en) 2009-04-29 2010-04-28 5,6,7,8-TETRAHYDRO[1,2,4]TRIAZOLO[4,3-a]PYRAZINE DERIVATIVES AS P2X7 MODULATORS

Country Status (5)

Country Link
US (1) US8501946B2 (ja)
EP (1) EP2424869B1 (ja)
JP (1) JP5654001B2 (ja)
ES (1) ES2590987T3 (ja)
WO (1) WO2010125102A1 (ja)

Cited By (30)

* Cited by examiner, † Cited by third party
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WO2011033055A1 (en) * 2009-09-21 2011-03-24 F. Hoffmann-La Roche Ag Fused triazole amines as p2x7 modulators
US20120157436A1 (en) * 2009-04-29 2012-06-21 David Kenneth Dean 5,6,7,8-TETRAHYDRO[1,2,4]TRIAZOLO[4,3-a]PYRAZINE DERIVATIVES AS P2X7 MODULATORS
JP2012525351A (ja) * 2009-04-30 2012-10-22 グラクソ グループ リミテッド Ｐ２Ｘ７調節因子としての５，６，７，８−テトラヒドロイミダゾ［１，２−ａ］ピラジン誘導体
WO2013050424A1 (en) * 2011-10-03 2013-04-11 Euroscreen S.A. NOVEL CHIRAL N-ACYL-5,6,7,(8-SUBSTITUTED)-TETRAHYDRO-[1,2,4]TRIAZOLO[4,3-a]PYRAZINES AS SELECTIVE NK-3 RECEPTOR ANTAGONISTS, PHARMACEUTICAL COMPOSITION, METHODS FOR USE IN NK-3 RECEPTOR MEDIATED DISORDERS AND CHIRAL SYNTHESIS THEREOF
EP2604265A1 (en) 2011-12-17 2013-06-19 Royal College of Surgeons in Ireland (RCSI) P2x7 antagonists as frontline or adjunctive treatment against status epilepticus
WO2014152621A1 (en) * 2013-03-14 2014-09-25 Janssen Pharmaceutica Nv P2x7 modulators
WO2014152537A1 (en) * 2013-03-14 2014-09-25 Janssen Pharmaceutica Nv P2x7 modulators
WO2014154897A1 (en) * 2013-03-29 2014-10-02 Euroscreen Sa NOVEL N-ACYL-(3-SUBSTITUTED)-(8-METHYL)-5,6-DIHYDRO-[1,2,4]TRIAZOLO[4,3-a]PYRAZINES AS SELECTIVE NK-3 RECEPTOR ANTAGONISTS, PHARMACEUTICAL COMPOSITION, METHODS FOR USE IN NK-3 RECEPTOR-MEDIATED DISORDERS
WO2014154896A1 (en) * 2013-03-29 2014-10-02 Euroscreen Sa NOVEL N-ACYL-(3-SUBSTITUTED)-5,6,7,8-TETRAHYDRO-[1,2,4]TRIAZOLO[4,3-a]PYRAZINES AS SELECTIVE NK-3 RECEPTOR ANTAGONISTS, PHARMACEUTICAL COMPOSITION, METHODS FOR USE IN NK-3 RECEPTOR-MEDIATED DISORDERS
WO2014154895A1 (en) 2013-03-29 2014-10-02 Euroscreen Sa NOVEL N-ACYL-(3-SUBSTITUTED)-(8-SUBSTITUTED)-5,6-DIHYDRO- [1,2,4]TRIAZOLO[4,3-a]PYRAZINES AS SELECTIVE NK-3 RECEPTOR ANTAGONISTS, PHARMACEUTICAL COMPOSITION, METHODS FOR USE IN NK-3 RECEPTOR-MEDIATED DISORDERS
US8871761B2 (en) 2010-04-02 2014-10-28 Euroscreen S.A. NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders
WO2016039977A1 (en) * 2014-09-12 2016-03-17 Janssen Pharmaceutica Nv P2x7 modulators
WO2016039983A1 (en) * 2014-09-12 2016-03-17 Janssen Pharmaceutica Nv P2x7 modulating n-acyl-triazolopyrazines
WO2016046398A1 (en) * 2014-09-25 2016-03-31 Euroscreen Sa Novel chiral synthesis of n-acyl-(3-substituted)-(8-substituted)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazines
US9464084B2 (en) 2013-03-14 2016-10-11 Janssen Pharmaceutica Nv P2X7 modulators
US9604982B2 (en) 2013-03-14 2017-03-28 Janssen Pharmaceutica Nv P2X7 modulators
US9688699B2 (en) 2014-02-19 2017-06-27 Bayer Pharma Aktiengesellschaft 3-(pyrimidine-2-yl)imidazo[1,2-a]pyridines
US9776997B2 (en) 2013-06-04 2017-10-03 Bayer Pharma Aktiengesellschaft 3-aryl-substituted imidazo[1,2-A]pyridines and their use
US10065960B2 (en) 2010-04-02 2018-09-04 Ogeda Sa NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders
US10183948B2 (en) 2013-03-29 2019-01-22 Ogeda Sa N-acyl-(3-substituted)-(8-substituted)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazines as selective NK-3 receptor antagonists
US10292970B2 (en) 2014-12-02 2019-05-21 Bayer Pharma Aktiengesellschaft Heteroaryl-substituted imidazo[1,2-A]pyridines and their use
WO2020211798A1 (zh) * 2019-04-16 2020-10-22 上海翰森生物医药科技有限公司 含二并环类衍生物抑制剂、其制备方法和应用
US11066409B2 (en) 2016-10-17 2021-07-20 Shionogi & Co., Ltd. Bicyclic nitrogen-containing heterocyclic derivatives and pharmaceutical composition comprising the same
US11124486B2 (en) 2015-04-24 2021-09-21 Shionogi & Co., Ltd. 6-membered heterocyclic derivatives and pharmaceutical composition comprising the same
CN113527307A (zh) * 2020-04-20 2021-10-22 上海翰森生物医药科技有限公司 含三唑基的并环类衍生物抑制剂、其制备方法和应用
CN113549074A (zh) * 2020-04-26 2021-10-26 上海翰森生物医药科技有限公司 含三唑基的并环类衍生物抑制剂、其制备方法和应用
US11597728B2 (en) 2018-09-28 2023-03-07 Janssen Pharmaceutica Nv Monoacylglycerol lipase modulators
US11820766B2 (en) 2018-09-28 2023-11-21 Janssen Pharmaceutica Nv Monoacylglycerol lipase modulators
US11839663B2 (en) 2019-09-30 2023-12-12 Janssen Pharmaceutica Nv Radiolabelled MGL pet ligands
US11891387B2 (en) 2020-03-26 2024-02-06 Janssen Pharmaceutica Nv Monoacylglycerol lipase modulators

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WO2014195321A1 (en) * 2013-06-04 2014-12-11 Acturum Life Science AB Triazole compounds and their use as gamma secretase modulators
EP3496716B1 (en) 2016-08-15 2021-11-03 Merck Sharp & Dohme Corp. Compounds useful for altering the levels of bile acids for the treatment of diabetes and cardiometabolic disease
WO2018034917A1 (en) * 2016-08-15 2018-02-22 Merck Sharp & Dohme Corp. Compounds useful for altering the levels of bile acids for the treatment of diabetes and cardiometabolic disease
WO2019145214A1 (en) * 2018-01-26 2019-08-01 Recordati Industria Chimica E Farmaceutica S.P.A TRIAZOLE, IMIDAZOLE AND PYRROLE CONDENSED PIPERAZINE DERIVATIVES AND THEIR USE AS MODULATORS OF mGlu5 RECEPTORS
EP3962493A2 (en) 2019-05-03 2022-03-09 Flagship Pioneering Innovations V, Inc. Methods of modulating immune activity/level of irf or sting or of treating cancer, comprising the administration of a sting modulator and/or purinergic receptor modulator or postcellular signaling factor

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Cited By (82)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8501946B2 (en) * 2009-04-29 2013-08-06 Glaxo Group Limited 5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrazine derivatives as P2X7 modulators
US20120157436A1 (en) * 2009-04-29 2012-06-21 David Kenneth Dean 5,6,7,8-TETRAHYDRO[1,2,4]TRIAZOLO[4,3-a]PYRAZINE DERIVATIVES AS P2X7 MODULATORS
JP2012525351A (ja) * 2009-04-30 2012-10-22 グラクソ グループ リミテッド Ｐ２Ｘ７調節因子としての５，６，７，８−テトラヒドロイミダゾ［１，２−ａ］ピラジン誘導体
WO2011033055A1 (en) * 2009-09-21 2011-03-24 F. Hoffmann-La Roche Ag Fused triazole amines as p2x7 modulators
US10065960B2 (en) 2010-04-02 2018-09-04 Ogeda Sa NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders
US9926325B2 (en) 2010-04-02 2018-03-27 Ogeda Sa NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders
US10544150B2 (en) 2010-04-02 2020-01-28 Ogeda Sa NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders
US8871761B2 (en) 2010-04-02 2014-10-28 Euroscreen S.A. NK-3 receptor selective antagonist compounds, pharmaceutical composition and methods for use in NK-3 receptors mediated disorders
AU2012320568C1 (en) * 2011-10-03 2018-07-19 Ogeda S.A. Novel chiral N-acyl-5,6,7,(8-substituted)-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazines as selective NK-3 receptor antagonists, pharmaceutical composition, methods for use in NK-3 receptor mediated disorders and chiral synthesis thereof
WO2013050424A1 (en) * 2011-10-03 2013-04-11 Euroscreen S.A. NOVEL CHIRAL N-ACYL-5,6,7,(8-SUBSTITUTED)-TETRAHYDRO-[1,2,4]TRIAZOLO[4,3-a]PYRAZINES AS SELECTIVE NK-3 RECEPTOR ANTAGONISTS, PHARMACEUTICAL COMPOSITION, METHODS FOR USE IN NK-3 RECEPTOR MEDIATED DISORDERS AND CHIRAL SYNTHESIS THEREOF
EA029340B1 (ru) * 2011-10-03 2018-03-30 Огеда Са ХИРАЛЬНЫЕ N-АЦИЛ-5,6,7,(8-ЗАМЕЩЕННЫЕ)-ТЕТРАГИДРО[1,2,4]ТРИАЗОЛО[4,3-a]ПИРАЗИНЫ КАК СЕЛЕКТИВНЫЕ АНТАГОНИСТЫ РЕЦЕПТОРА NK-3, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБЫ ПРИМЕНЕНИЯ ПРИ НАРУШЕНИЯХ, ОПОСРЕДОВАННЫХ NK-3 РЕЦЕПТОРАМИ, И ИХ ХИРАЛЬНЫЙ СИНТЕЗ
US10941151B2 (en) 2011-10-03 2021-03-09 Ogeda Sa Chiral N-acyl-5,6,7(8-substituted)-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazines as selective NK-3 receptor antagonists, pharmaceutical composition, methods for use in NK-3 receptor mediated disorders and chiral synthesis thereof
CN103906750A (zh) * 2011-10-03 2014-07-02 欧洲筛选有限公司 作为选择性NK-3受体拮抗剂的新型手性N-酰基-5,6,7,(8-取代的)-四氢-[1,2,4]三唑并[4,3-a]吡嗪、药物组合物、用于NK-3受体介导的疾病中的方法及其手性合成
US10065961B2 (en) 2011-10-03 2018-09-04 Ogeda Sa. Chiral N-acyl-5,6,7,(8-substituted)-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazines as selective NK-3 receptor antagonists, pharmaceutical composition, methods for use in NK-3 receptor mediated disorders and chiral synthesis thereof
EP3029042A1 (en) * 2011-10-03 2016-06-08 Euroscreen S.A. Novel chiral n-acyl-5,6,7,(8-substituted)-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazines as selective nk-3 receptor antagonists, pharmaceutical composition, methods for use in nk-3 receptor mediated disorders and chiral synthesis thereof
AU2012320568B2 (en) * 2011-10-03 2017-07-06 Ogeda S.A. Novel chiral N-acyl-5,6,7,(8-substituted)-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazines as selective NK-3 receptor antagonists, pharmaceutical composition, methods for use in NK-3 receptor mediated disorders and chiral synthesis thereof
US10683295B2 (en) 2011-10-03 2020-06-16 Ogeda Sa Chiral N-acyl-5,6,7(8-substituted)-tetrahydro-[1,2,4]triazolo[4,3-A]pyrazines as selective NK-3 receptor antagonists, pharmaceutical composition, methods for use in NK-3 receptor mediated disorders and chiral synthesis thereof
US9475814B2 (en) 2011-10-03 2016-10-25 Euroscreen S.A. Chiral N-acyl-5,6,7(8-substituted)-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazines as selective NK-3 receptor antagonists, pharmaceutical composition, methods for use in NK-3 receptor mediated disorders and chiral synthesis thereof
WO2013087943A1 (en) 2011-12-17 2013-06-20 Royal College Of Surgeons In Ireland (Rcsi) P2x7 antagonists as frontline or adjunctive treatment against status epilepticus
EP2604265A1 (en) 2011-12-17 2013-06-19 Royal College of Surgeons in Ireland (RCSI) P2x7 antagonists as frontline or adjunctive treatment against status epilepticus
WO2014152537A1 (en) * 2013-03-14 2014-09-25 Janssen Pharmaceutica Nv P2x7 modulators
JP2016513698A (ja) * 2013-03-14 2016-05-16 ヤンセン ファーマシューティカ エヌ．ベー． Ｐ２ｘ７モジュレーター
US10150765B2 (en) 2013-03-14 2018-12-11 Janssen Pharmaceutica Nv P2X7 modulators
US9464084B2 (en) 2013-03-14 2016-10-11 Janssen Pharmaceutica Nv P2X7 modulators
US10323032B2 (en) 2013-03-14 2019-06-18 Janssen Pharmaceutica Nv P2X7 Modulators
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